Freewill, Determinism, and Entropy...Oh My!

A street car approaches a set of crossing tracks, with road signs and buildings in the background.
For a time, my career train was on tracks like these. Photo by Fons Heijnsbroek / Unsplash

Or: more rambling thoughts about careerism, changing tracks, and whether or not any of it is really our decision.

Quick Ed. note: this one got away from me. I like the point I eventually get to, so I’m leaving it as is to give you an idea of how these things swirl around in my brain and eventually come out as written essays. Whether the words are in the right order or not I leave up to you.


"The ability to differentiate between what we want and what we want to want." That is the definition of 'free will.'"

Source unclear, quoted by Angela Duckworth on the No Stupid Questions podcast

What I like about this quote is how simple it seems on the surface, but when you stay with it for a moment you see how incredibly complex the difference is. Self-image comes into play, as do cultural norms, family history, personal finance, and so many sub-specialties of psychology I lose track before I can even start a list.

This is also something I've struggled with, well...forever. How many purchases can I trace to a thing I wanted to want? Something I believed "someone like me" should want. my first mountain bike, my touring kayak, my second Tacoma, etc...etc…etc.

When I look at this through the lens of what I've learned about myself over the last, say, 5-7 years—that's when the insanity of it hits.

"Someone like me" isn’t a thing.

At least, not a thing I need to be spending my limited time and energy worrying about. I am me. I am the only someone like me that I need to care about or whose opinion matters to this discussion.

What’s the difference? Why does it matter if I wanted, or just thought I wanted, or even thought I should want those things? Well, for starters, I never did camp in that Tacoma. It gets more salient when you expand the discussion to areas other than consumerism. Take that mythical thing, the "work-life balance," or careerism, for one example.

I’m a writer. Currently freelance, but until late in '23 for a tech startup in the overlapping space where freight forwarding and technology meet. I used to be IT support. I entered adulthood with a degree in Anthropology, and several years ago earned a Graduate Certificate in Coaching. How did that particular chain of events come to pass? Honestly? I’m still working that out.

When I graduated and started looking for work, you can imagine what I found in late 90s Seattle as a brand new graduate with a liberal arts degree and no ability to write code. Right. I took what I could get. I’m shortcutting a bit here since I didn’t land my first “real” job for several years, suffice it to say there was the requisite time spent as a barista, or ski instructor, you get the picture.

As for that first “real” job, I interviewed to be a technical instructor for a large real estate company, figuring my experience as a ski instructor might serve me well. Nope, but they did hire me to answer the phones for their internal tech department. From there, my career fate was sealed. I was now IT Guy.

Little did I know it at the time, but I was also embarking on more than a decade of career entropy.

It was miserable.

I was miserable.

I truly have no idea how those who knew me at the time could stand to be in the same room as me.


A brief aside to further explore the notion of free will: Neo-Freudians work from a belief that all humans are born with the ability and potential to govern themselves, but then we have it beat out of us by the guiding culture we’re surrounded by.

That’s pretty much what I experienced. After several years in IT, the assumption became that I was what I was—IT Guy. So when I started looking to jump clear of that career train, I couldn’t get past the tracks. In the end, it took more than 15 years and several aborted attempts to make the pivot to writing.

Which I finally did, at age 40.

I've written about my mid-life pivot here and here, so I'll keep today about what happens when we become complacent to the cultural assumptions and standards we're surrounded by. I will offer a reading recommendation, however, Pivot by Jenny Blake. Even if you’re not looking to make a career shift, it’s a beautiful book full of broader work-life advice.

My early attempts at extricating myself from the IT world ended with me tucking my tail between my legs and signing up with yet another IT contracting agency, hoping to be able to make rent that month. Why? Mostly because nobody I approached could see past the outward trappings of my experience. I was IT guy. Also because I was unable to sell what I was capable of, rather than simply pointing at what I had already done.

This brings up interesting directions for the nature vs nurture debate, but I digress. Again.

Society clings to the old pattern of “graduate, get a job, work ’til retirement, done.” But that model doesn’t work anymore. It hasn’t since well before I graduated in the ‘90s—if anyone would pause long enough to think about it. Given the modern rise of gig work, the millennial generation’s focus on values and meaning, and my own generation’s slow-dawning realization that we’re pretty much screwed on the retirement front—what it means to have a career in 2021 bears strikingly little resemblance to what it meant even in 2011, let alone 2001, 1991, 1981, etc.

So that’s a cultural construct that’s outlived its usefulness.

Bringing this back around full circle to free will (or close enough to full circle, though I’m becoming less certain about the comparison to determinism the more I write), step back and look at some of the things you do in an average day. Why are you doing them?

Because your boss said to?

Because that’s how you’ve always done it?

Or because you actively want to?

I wrote the first draft of this piece from a patio next to a Canadian ski hill in early spring because that last job with the startup came with some incredible benefits I could never have imagined I would have when I started writing full-time. But I kept with it, making my pivot incrementally (fodder for many later pieces, I assure you), and found myself in a pretty awesome place when I emerged on the other side.

What can you do today to express your free will? Be it in a creative, career, or relationship area of your life? I bet if you looked objectively, there are some things you’d like to change, too.